Lido/Flight is a software build by Lufthansa Systems over the last 20+ years and is used by more than 80 airlines around the world. Its purpose is to calculate an optimal trajectory for a flight event. Due to the grown monolithic architecture, it had become very costly to maintain and enhance the software. We decided to change the architecture towards a microservices architecture and the way we build our software should follow the principals of Disciplined Agile Delivery. Mid of 2016 we have been through the first steps of our agile transformation and faced issues to rollout our software to the customers. Therefore, we decided to have a deeper look into DevOps practices and principles. Management agreed to run this as a project and I was assigned as project manager. Out of this role I will share the insights how we stated the project, what we learned during the project and what I would do different if I would have the chance to do it again.